메뉴 건너뛰기




Volumn 39, Issue 8, 1996, Pages 1575-1581

Synthesis and biological evaluation of naphthyldesferrithiocin iron chelators

Author keywords

[No Author keywords available]

Indexed keywords

2 (2 HYDROXY 1 NAPHTHYL) 2 THIAZOLINE 4 CARBOXYLIC ACID; 2 (3 HYDROXY 2 NAPHTHYL) 2 THIAZOLINE 4 CARBOXYLIC ACID; CHELATING AGENT; DEFERRIFERRITHIOCIN; IRON CHELATING FACTOR; UNCLASSIFIED DRUG;

EID: 0029963339     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9508752     Document Type: Article
Times cited : (42)

References (46)
  • 1
    • 33845559030 scopus 로고
    • Coordination Chemistry and Microbial Iron Transport
    • Raymond, K. N.; Carrano, C. J. Coordination Chemistry and Microbial Iron Transport. Acc. Chem. Res. 1979, 12, 183-190.
    • (1979) Acc. Chem. Res. , vol.12 , pp. 183-190
    • Raymond, K.N.1    Carrano, C.J.2
  • 2
    • 0021193844 scopus 로고
    • Transferrin: Physiologic Behavior and Clinical Implications
    • Huebers, H. A.; Finch, C. A. Transferrin: Physiologic Behavior and Clinical Implications. Blood 1984, 64, 763-767.
    • (1984) Blood , vol.64 , pp. 763-767
    • Huebers, H.A.1    Finch, C.A.2
  • 4
    • 0019746191 scopus 로고
    • Bioavailability of Dietary Iron in Man
    • Hallberg, L. Bioavailability of Dietary Iron in Man. Ann. Rev. Nutr. 1981, 1, 123-147.
    • (1981) Ann. Rev. Nutr. , vol.1 , pp. 123-147
    • Hallberg, L.1
  • 5
    • 0020035215 scopus 로고
    • Perspectives in Iron Metabolism
    • Finch, C. A.; Huebers, H. Perspectives in Iron Metabolism. N. Engl. J. Med. 1982, 306, 1520-1528.
    • (1982) N. Engl. J. Med. , vol.306 , pp. 1520-1528
    • Finch, C.A.1    Huebers, H.2
  • 7
    • 0001109933 scopus 로고
    • Molecular Mechanisms of Iron Metabolism
    • Stamatoyannopoulos, G., Nienhuis, A. W., Leder, P., Majerus, P. W., Eds.; W. B. Saunders: Philadelphia
    • Seligman, P. A.; Klausner, R. D.; Huebers, H. A. Molecular Mechanisms of Iron Metabolism. In The Molecular Basis of Blood Diseases; Stamatoyannopoulos, G., Nienhuis, A. W., Leder, P., Majerus, P. W., Eds.; W. B. Saunders: Philadelphia, 1987; p 219.
    • (1987) The Molecular Basis of Blood Diseases , pp. 219
    • Seligman, P.A.1    Klausner, R.D.2    Huebers, H.A.3
  • 8
    • 0021856398 scopus 로고
    • The Role of Iron in Ferritin- and Haemosiderin-Mediated Lipid Peroxidation in Liposomes
    • O'Connell, M. J.; Ward, R. J.; Baum, H.; Peters, T. J. The Role of Iron in Ferritin- and Haemosiderin-Mediated Lipid Peroxidation in Liposomes. Biochem J. 1985, 229, 135-139.
    • (1985) Biochem J. , vol.229 , pp. 135-139
    • O'Connell, M.J.1    Ward, R.J.2    Baum, H.3    Peters, T.J.4
  • 9
    • 0021993608 scopus 로고
    • Ferritin and Superoxide-Dependent Lipid Peroxidation
    • Thomas, C. E.; Morehouse, L. A.; Aust, S. D. Ferritin and Superoxide-Dependent Lipid Peroxidation. J. Biol. Chem. 1985, 260, 3275-3280.
    • (1985) J. Biol. Chem. , vol.260 , pp. 3275-3280
    • Thomas, C.E.1    Morehouse, L.A.2    Aust, S.D.3
  • 10
    • 0028033797 scopus 로고
    • Hereditary Hemochromatosis. Detecting and Correcting Iron Overload
    • Olynyk, J. K.; Bacon, B. R. Hereditary Hemochromatosis. Detecting and Correcting Iron Overload. Postgrad. Med. 1994, 96, 151-165.
    • (1994) Postgrad. Med. , vol.96 , pp. 151-165
    • Olynyk, J.K.1    Bacon, B.R.2
  • 12
    • 0026938837 scopus 로고
    • Diagnosis, Treatment, and Nursing Management of the Patient with Hemochromatosis
    • Keller, J. F.; Blausey, L. A. Diagnosis, Treatment, and Nursing Management of the Patient with Hemochromatosis. Oncol. Nurs. Forum 1992, 19, 1359-1365.
    • (1992) Oncol. Nurs. Forum , vol.19 , pp. 1359-1365
    • Keller, J.F.1    Blausey, L.A.2
  • 14
    • 0345155952 scopus 로고
    • Thalassemia and Desferrioxamine (Desferal) - Introductory Remarks, and Clinical Laboratory Observations
    • Aksov, M., Birdwood, G. F. B., Eds.; Berne: Huber
    • Aksoy, M.; Seyithanoglu, B. Y.; Bozbora, A. Thalassemia and Desferrioxamine (Desferal) - Introductory Remarks, and Clinical Laboratory Observations. In Hypertension and Iron Chelation in Thalassemia; Aksov, M., Birdwood, G. F. B., Eds.; Berne: Huber, 1984; p 11.
    • (1984) Hypertension and Iron Chelation in Thalassemia , pp. 11
    • Aksoy, M.1    Seyithanoglu, B.Y.2    Bozbora, A.3
  • 16
    • 85047691907 scopus 로고
    • The Management of Iron Chelation Therapy
    • Pippard, M. J.; Callender, S. T. The Management of Iron Chelation Therapy. Br. J. Haematol. 1983, 54, 503-507.
    • (1983) Br. J. Haematol. , vol.54 , pp. 503-507
    • Pippard, M.J.1    Callender, S.T.2
  • 18
    • 0002884546 scopus 로고
    • Industrial Aspects of Iron Chelators: Pharmaceutical Applications
    • Spik, G., Ed.; Elsevier: Amsterdam, The Netherlands
    • Peter, H. H.; Industrial Aspects of Iron Chelators: Pharmaceutical Applications. In Proteins Iron Storage Transp., Proc. Inter. Conf. Proteins Iron Metab., 7th; Spik, G., Ed.; Elsevier: Amsterdam, The Netherlands, 1985; p 293.
    • (1985) Proteins Iron Storage Transp., Proc. Inter. Conf. Proteins Iron Metab., 7th , pp. 293
    • Peter, H.H.1
  • 19
    • 84984088084 scopus 로고
    • Hydroxamate Complexes. III. Iron (III) Exchange between Sideramines and Complexones. A Discussion of the Formation Constants of the Hydroxamate Complexes
    • Anderegg, G.; L'Eplattenier, F.; Schwarzenbach, G. Hydroxamate Complexes. III. Iron (III) Exchange between Sideramines and Complexones. A Discussion of the Formation Constants of the Hydroxamate Complexes. Helv. Chim. Acta 1963, 46, 1409-1422.
    • (1963) Helv. Chim. Acta , vol.46 , pp. 1409-1422
    • Anderegg, G.1    L'Eplattenier, F.2    Schwarzenbach, G.3
  • 21
    • 0025781930 scopus 로고
    • Treatment of Chronic Iron Overload
    • Kirking, M. H. Treatment of Chronic Iron Overload. Clin. Pharmacol. 1991, 10, 775-783.
    • (1991) Clin. Pharmacol. , vol.10 , pp. 775-783
    • Kirking, M.H.1
  • 22
    • 0018394556 scopus 로고
    • Mobilization of Iron from Reticulocytes. Identification of Pyridoxal Isonicotinoyl Hydrazone as a New Iron Chelating Agent
    • Ponka, P.; Borova, J.; Neuwirt, J.; Fuchs, O. Mobilization of Iron from Reticulocytes. Identification of Pyridoxal Isonicotinoyl Hydrazone as a New Iron Chelating Agent. FEBS Lett. 1979, 97, 317-321.
    • (1979) FEBS Lett. , vol.97 , pp. 317-321
    • Ponka, P.1    Borova, J.2    Neuwirt, J.3    Fuchs, O.4
  • 23
    • 0027463766 scopus 로고
    • Specific Sequestering Agents for the Actinides. 21. Synthesis and Initial Biological Testing of Octadentate Mixed Catecholate-Hydroxypyridinonate Ligands
    • Uhlir, L. C.; Durbin, P. W.; Jeung, N.; Raymond, K. N. Specific Sequestering Agents for the Actinides. 21. Synthesis and Initial Biological Testing of Octadentate Mixed Catecholate-Hydroxypyridinonate Ligands. J. Med. Chem. 1993, 36, 504-509.
    • (1993) J. Med. Chem. , vol.36 , pp. 504-509
    • Uhlir, L.C.1    Durbin, P.W.2    Jeung, N.3    Raymond, K.N.4
  • 24
    • 0023214937 scopus 로고
    • 1,2-Dimethyl-3-hydroxypyrid-4-one, an Orally Active Chelator for Treatment of Iron Overload
    • Kontoghiorghes, G. J.; Aldouri, M. A.; Sheppard, L.; Hoffbrand, A. V. 1,2-Dimethyl-3-hydroxypyrid-4-one, an Orally Active Chelator for Treatment of Iron Overload. Lancet 1987, 1, 1294-1295.
    • (1987) Lancet , vol.1 , pp. 1294-1295
    • Kontoghiorghes, G.J.1    Aldouri, M.A.2    Sheppard, L.3    Hoffbrand, A.V.4
  • 25
    • 0025534402 scopus 로고
    • HBED: A Potential Oral Iron Chelator
    • Grady, R. W.; Hershko, C. HBED: A Potential Oral Iron Chelator. Ann. N. Y. Acad. Sci. 1990, 612, 361-368.
    • (1990) Ann. N. Y. Acad. Sci. , vol.612 , pp. 361-368
    • Grady, R.W.1    Hershko, C.2
  • 26
    • 0018193504 scopus 로고
    • Feasibility of Enterochelin as an Iron-Chelating Drug: Studies with Human Serum and a Mouse Model System
    • Guterman, S. K.; Morris, P. M.; Tannenberg, W. J. K. Feasibility of Enterochelin as an Iron-Chelating Drug: Studies with Human Serum and a Mouse Model System. Gen. Pharmacol. 1978, 9, 123-127.
    • (1978) Gen. Pharmacol. , vol.9 , pp. 123-127
    • Guterman, S.K.1    Morris, P.M.2    Tannenberg, W.J.K.3
  • 28
    • 0002553989 scopus 로고
    • Synthesis and Solution Structure of Microbial Siderophores
    • Bergeron, R. J. Synthesis and Solution Structure of Microbial Siderophores. Chem. Rev. 1984, 84, 587-602.
    • (1984) Chem. Rev. , vol.84 , pp. 587-602
    • Bergeron, R.J.1
  • 29
    • 85053654339 scopus 로고
    • Synthesis of Catecholamide and Hydroxamate Siderophores
    • Winkelmann, G., Ed.; CRC Press: Boca Raton, FL
    • Bergeron, R. J.; McManis, J. S. Synthesis of Catecholamide and Hydroxamate Siderophores. In Handbook of Microbial Iron Chelates; Winkelmann, G., Ed.; CRC Press: Boca Raton, FL, 1981; pp 271-307.
    • (1981) Handbook of Microbial Iron Chelates , pp. 271-307
    • Bergeron, R.J.1    McManis, J.S.2
  • 30
    • 0019588236 scopus 로고
    • Pyochelin: Novel Structure of an Iron-Chelating Growth Promoter for Pseudomonas aeruginosa
    • Cox, C. D ; Rinehart, K L., Jr.; Moore, M. L.; Cook, J. C., Jr. Pyochelin: Novel Structure of an Iron-Chelating Growth Promoter for Pseudomonas aeruginosa. Proc. Natl. Acad. Sci. U.S.A. 1981, 78, 4256-4260.
    • (1981) Proc. Natl. Acad. Sci. U.S.A. , vol.78 , pp. 4256-4260
    • Cox, C.D.1    Rinehart Jr., K.L.2    Moore, M.L.3    Cook Jr., J.C.4
  • 31
    • 0024575874 scopus 로고
    • Total Synthesis and Absolute Configuration of Rhizobactin. A Structurally Novel Siderophore
    • Smith, M. J. Total Synthesis and Absolute Configuration of Rhizobactin. a Structurally Novel Siderophore. Tetrahedron Lett. 1989, 30, 313-316.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 313-316
    • Smith, M.J.1
  • 32
    • 84985071864 scopus 로고
    • Metabolites of Microorganisms. Part 193. Ferrithiocin
    • Naegeli, H.-U.; Zaehner, H. Metabolites of Microorganisms. Part 193. Ferrithiocin. Helv. Chim. Acta 1980, 63, 1400-1406.
    • (1980) Helv. Chim. Acta , vol.63 , pp. 1400-1406
    • Naegeli, H.-U.1    Zaehner, H.2
  • 33
    • 0025088608 scopus 로고
    • Metal Complex Formation of a New Siderophore Desferrithiocin and of Three Related Ligands
    • Anderegg, G.; Raeber, M. Metal Complex Formation of a New Siderophore Desferrithiocin and of Three Related Ligands. J. Chem. Soc., Chem. Commun. 1990, 1194-1196.
    • (1990) J. Chem. Soc., Chem. Commun. , pp. 1194-1196
    • Anderegg, G.1    Raeber, M.2
  • 34
    • 0023037399 scopus 로고
    • An Animal Model of Iron Overload and its Application to Study Hepatic Ferritin Iron Mobilization by Chelators
    • Longueville, A.; Crichton, R. R. An Animal Model of Iron Overload and its Application to Study Hepatic Ferritin Iron Mobilization by Chelators. Biochem. Pharmacol. 1986, 35, 3669-3678.
    • (1986) Biochem. Pharmacol. , vol.35 , pp. 3669-3678
    • Longueville, A.1    Crichton, R.R.2
  • 37
    • 0027401142 scopus 로고
    • A Comparative Study of the Iron-Clearing Properties of Desferrithiocin Analogues with Desferrioxamine B in a Cebus Monkey Model
    • Bergeron, R. J.; Streiff, R. R.; Creary, E. A.; Daniels, R. D., Jr.; King, W.; Luchetta, G.; Wiegand, J.; Moerker, T.; Peter, H. H. A Comparative Study of the Iron-Clearing Properties of Desferrithiocin Analogues with Desferrioxamine B in a Cebus Monkey Model. Blood 1993, 81, 2166-2173.
    • (1993) Blood , vol.81 , pp. 2166-2173
    • Bergeron, R.J.1    Streiff, R.R.2    Creary, E.A.3    Daniels Jr., R.D.4    King, W.5    Luchetta, G.6    Wiegand, J.7    Moerker, T.8    Peter, H.H.9
  • 38
    • 0026520355 scopus 로고
    • A Comparison of the Iron-Clearing Properties of 1,2-Dimethyl-3-hydroxypyrid-4-one, 1,2-Diethyl-3-hydroxypyrid-4-one and Deferoxamine
    • Bergeron, R. J.; Streiff, R. R.; Wiegand, J.; Luchetta, G.; Creary, E. A.; Peter, H. H. A Comparison of the Iron-Clearing Properties of 1,2-Dimethyl-3-hydroxypyrid-4-one, 1,2-Diethyl-3-hydroxypyrid-4-one and Deferoxamine. Blood 1992, 79, 1882-1890.
    • (1992) Blood , vol.79 , pp. 1882-1890
    • Bergeron, R.J.1    Streiff, R.R.2    Wiegand, J.3    Luchetta, G.4    Creary, E.A.5    Peter, H.H.6
  • 39
    • 0025288378 scopus 로고
    • Coordination Chemistry of Microbial Iron Transport. 42. Structural and Spectroscopic Characterization of Diastereomeric Cr-(III) and Co(III) Complexes of Desferrithiocin
    • Hahn, F. E.; McMurry, T. J.; Hugi, A.; Raymond, K. N. Coordination Chemistry of Microbial Iron Transport. 42. Structural and Spectroscopic Characterization of Diastereomeric Cr-(III) and Co(III) Complexes of Desferrithiocin. J. Am. Chem. Soc. 1990, 112, 1854-1860.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 1854-1860
    • Hahn, F.E.1    McMurry, T.J.2    Hugi, A.3    Raymond, K.N.4
  • 41
    • 55549131598 scopus 로고
    • Derivatives of 6-Aminopenicillanic Acid. Part IV. Analogues of 2,6-Dimethoxyphenylpenicillin in the Naphthalene and Quinoline Series
    • Brain, E. G.; Doyle, F. P.; Mehta, M. D.; Miller, D.; Nayler, J. H. C.; Stove, E. R. Derivatives of 6-Aminopenicillanic Acid. Part IV. Analogues of 2,6-Dimethoxyphenylpenicillin in the Naphthalene and Quinoline Series. J. Chem. Soc. 1963, 491-497.
    • (1963) J. Chem. Soc. , pp. 491-497
    • Brain, E.G.1    Doyle, F.P.2    Mehta, M.D.3    Miller, D.4    Nayler, J.H.C.5    Stove, E.R.6
  • 42
    • 0001118419 scopus 로고
    • Preparation of Carboxylic Acids from Aldehydes (Including Hydroxylated Benzaldehydes) by Oxidation with Chlorite
    • Lindgren, B. O.; Nilsson, T. Preparation of Carboxylic Acids from Aldehydes (Including Hydroxylated Benzaldehydes) by Oxidation with Chlorite. Acta Chem. Scand. 1973, 27, 888-890.
    • (1973) Acta Chem. Scand. , vol.27 , pp. 888-890
    • Lindgren, B.O.1    Nilsson, T.2
  • 43
    • 0001711883 scopus 로고
    • An Efficient Total Synthesis of Agrobactin and Its Gallium(III) Chelate
    • Bergeron, R. J.; McManis, J. S.; Dionis, J. B.; Garlich, J. R. An Efficient Total Synthesis of Agrobactin and Its Gallium(III) Chelate. J. Org. Chem. 1985, 50, 2780-2782.
    • (1985) J. Org. Chem. , vol.50 , pp. 2780-2782
    • Bergeron, R.J.1    McManis, J.S.2    Dionis, J.B.3    Garlich, J.R.4
  • 44
    • 0001511660 scopus 로고
    • Formation and Stability of Inorganic Complexes in Solution
    • Job, P. Formation and Stability of Inorganic Complexes in Solution. Ann. Chim. (Paris) 1928, 9, 113-203.
    • (1928) Ann. Chim. (Paris) , vol.9 , pp. 113-203
    • Job, P.1
  • 45
    • 15844427489 scopus 로고
    • Job's Method of Continuous Variations with Ion Exchange for the Study of Complexes in Solution
    • Bukata, S.; Marinsky, J. A. Job's Method of Continuous Variations with Ion Exchange for the Study of Complexes in Solution. J. Phys. Chem. 1964, 68, 258-260.
    • (1964) J. Phys. Chem. , vol.68 , pp. 258-260
    • Bukata, S.1    Marinsky, J.A.2
  • 46
    • 0012243705 scopus 로고
    • The Constitution of Naphthalenes and their Derivatives
    • Lesser, R ; Kranepuhl, E.; Gad, G. The Constitution of Naphthalenes and their Derivatives. Chem. Ber. 1925, 58, 2109-2124.
    • (1925) Chem. Ber. , vol.58 , pp. 2109-2124
    • Lesser, R.1    Kranepuhl, E.2    Gad, G.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.